Initially looking at Vegas but would really like some help thinking outside the box on places I would never have considered without help.

If you want a cheap but really nice Midwest getaway... I love the Missouri wine country. I convinced my buddy's parents to try it out one year and now they go all the time. What's cool about that is that they used to live near Napa and think that Hermann and the Katy Trail area remind them of all of Napa's early charm before it became popular and douchey. Great trip in the spring but even better in the fall.

If you're big into music there is always Austin for various music festivals. You have SXSW in March, ACL in September. Austin's just a fun town in general.

New Orleans is always fun if you've never been before. Same for Key West. Same for DC.

If you want a cheap but really nice Midwest getaway... I love the Missouri wine country. I convinced my buddy's parents to try it out one year and now they go all the time. What's cool about that is that they used to live near Napa and think that Hermann and the Katy Trail area remind them of all of Napa's early charm before it became popular and douchey. Great trip in the spring but even better in the fall.

If you're big into music there is always Austin for various music festivals. You have SXSW in March, ACL in September. Austin's just a fun town in general.

New Orleans is always fun if you've never been before. Same for Key West. Same for DC.

Late Spring in New York is another great option.

I've never had much desire for visiting NY but I would like to see the WTC site someday. Is NY really a long weekend getaway type trip though?

My top ten (from the perspective of someone born and raised in Philly and living near DC eliminating KC, StL and Denver which are high on my list): Boston in early autumn, Seattle/Portland/Vancouver whenever it's relatively dry, San Diego in January (beach+city+Tijuana), Miami/FL Keys, Albequerque/Santa Fe, Arizona, Yellowstone, Dallas, San Francisco, New York in Spring. For the record, DC is a wonderful pace to visit during the Cherry Blossom Festival in early spring.